HCID 59596691, compound → HCID 59596702, compound

HRID 2264827Notes

Reaction equation

HRID 2264827 reaction equation
[C:1]1(/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:18]([C:27]([O:29][CH3:30])=[O:28])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[C:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[N:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:18]([C:27]([O:29][CH3:30])=[O:28])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 59596691HCID 59596691, compound

Product 1

HCID 59596702HCID 59596702, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(1,1-dimethylethyl) 2-methyl (2S,5R)-5-{4-[(E)-2-phenylethenyl]phenyl}-1,2-pyrrolidinedicarboxylate (D79, 50 mg, 0.12 mmol) in methanol was added palladium (10 mg, 10 wt. % dry basis on activated carbon) and the mixture was stirred under hydrogen atmosphere (1 atm) for 4 h. A further addition of catalyst (20 mg) was required before the reaction was complete (as shown by HPLC). The catalyst was filtered off, the solvent removed under reduced pressure affording the title compound as a colourless oil (45 mg, 92%). Rt (HPLC): 7.04 min; MS: (ES/+) m/z: 432 [M+Na] C25H31NO4 requires 409.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4fb85bf45e5c414fa35ef9af2c9fe9c4
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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